433 Gilbert Road, FL433 Gilbert Road, FL433 Gilbert Road, FL
Stellar MLS
1 / 36

$675,000

433 Gilbert Road

Winter Park, FL 32792

Listing updated: August 5, 2026 at 2:29 PM ET

Active
Stellar MLSListing courtesy of Keller Williams Winter Park · Amy Turner · MLS #O6428430 · Active · 407-545-6430
3
Beds
2
Baths
1,770
Sq Ft
0.21
Acres
1965
Built
Private pool$381/sqft
Single Family Residence

Property type

1965

Year built

9,230 sqft

Lot size

$381

Price / sq ft

No HOA

HOA dues

9

Days on market

2

Garage spaces

X

Flood zone

About this home

Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

Estimated monthly payment

Principal & interest$3,413
Property taxes$336
Home insurance (est.)$309

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history9 days on market

  1. Status: Active
    Jul 27, 2026
  2. Listed$675,000
    Jul 27, 2026
  3. Price increased$675,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
9
Subdivision
Winter Park Pines
County
Orange
Year built
1965
Living area
1,770 sq ft
Price/sq ft
$381
Building area
2,754 sq ft (Public Records)
Lot size
9,230 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12095C0255F)
Garage
2 spaces
Pool
Private pool
Annual taxes
$4,032 (2025)
Parcel #
09-22-30-9664-04-310
Zoning
R-1A
MLS #
O6428430

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Interior Details

Bedrooms
3
Full bathrooms
2
Flooring
Ceramic Tile, Laminate, Terrazzo
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Interior features
Built-in Features, Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry
In Garage
Stories / Levels
One
Direction faces
East

Heating & Cooling

Heating
Electric
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Driveway, Garage Door Opener, On Street, Workshop in Garage

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
8-12 Months
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Buyer to verify lease restrictions with Orange County.

Exterior & Construction

Exterior features
French Doors, Private Mailbox, Rain Gutters, Sidewalk
Construction materials
Block
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Asphalt, Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Electricity Connected, Sewer Connected, Water Connected

Community

Pets allowed
Cats OK, Dogs OK, Yes

Schools

ElementaryCBrookshire ElemGreatSchools ↗
MiddleAGlenridge MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Living RoomFirst21x12
Family RoomFirst16x15
KitchenFirst13x11
Dining RoomFirst12x10
Primary BedroomFirst15x12
Primary BathroomFirst
Bedroom 2First18x11
Bedroom 3First15x11
Bathroom 2First
Balcony/Porch/LanaiFirst29x9

Listing Details

Listing date
2026-07-25
On market date
2026-07-27
Original list price
$675,000
Occupant type
Owner
MLS area
32792 - Winter Park/Aloma
Listing AOR
Orlando Regional
Status changed
2026-07-27
Tax legal description
WINTER PARK PINES UNIT 5 Z/91 LOT 31 BLKD

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From downtown Winter Park, head east on Fairbanks Ave. Turn right on N Ranger Road, right on Bower Road and wind the left on Gilbert Road. 433 Gilbert Road will be on your right.

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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